Sodium hydride → 2-(2,3-dihydro-1H-inden-2-yl)oxirane

HRID 1280747Notes

Reaction equation

HRID 1280747 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[CH:18]=[O:19]>CS(C)=O>[CH2:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH:10]1[CH:18]1[CH2:4][O:19]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 117447712,3-Dihydro-1H-indene-2-carbaldehyde

Product 1

HCID 184258062-(2,3-dihydro-1H-inden-2-yl)oxiraneYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture containing NaH (9.8 mg, 0.2 mmol) and trimethylsulfoxoniumiodide (57.8 mg, 0.26 mmol) was added slowly DMSO (0.44 ml). After 30 minutes stirring at room temperature, a solution of indan-2-carbaldehyde (32 mg, 0.22 mmol) in DMSO (0.1 ml) was added. The reaction mixture was stirred 18 hours at room temperature and then quenched with H2O. The aqueous phase was extracted with ethylacetate, combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 98:2) to provide (RS)-2-indan-2-yl-oxirane (9 mg, 26%) as a colorless oil, MS: m/e=160.0 (M+).

Workup

  1. stirringThe reaction mixture was stirred 18 hours at room temperature
  2. customquenched with H2O
  3. extractionThe aqueous phase was extracted with ethylacetate
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel (hexane-ethylacetate 98:2)

Sources & evidence

ORD record
ord-89d3b68031d34472a60483b49d7174df
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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